1. Field of the Invention
The invention is directed to cationic fluorinated alcohols, compositions containing the same, and methods for treating surfaces such as hair and skin.
2. Description of Related Art
Hair conditioning refers to the process of imparting attributes such as smoothness, softness, and ease of styling to hair. Conditioning may also reduce a feeling of dryness and impart shine. Both damaged and normal hair require conditioning, however, there is a greater need of conditioning for damaged hair due to the negative attributes it imparts. There is no single sensory attribute that equates with the perception of damage, rather it is associated with a combination of tactile and visual properties. For example, damaged hair in general is more hydrophilic leaving it susceptible to moisture flux which increases its propensity for swelling and breakage leading to a rough texture. Additionally, damaged hair tends to have a duller appearance due to the scattering of light from its rough, non-uniform surface. Hair damage may be caused by environmental factors, such as chemical attack from bleaches, dyes and pollutants, photodamage from the sun, heat damage from a dryer or flat iron, or mechanical damage from styling. However, a perception of damage may also arise when hair has not been subject to these environmental factors, but from the hair being coarse or varied in lipid content and specific lipid composition. Improving upon benefits such as hydrophobicity, shine and tactile properties leads to the perception of healthier, more conditioned hair.
Among the best known hair conditioners are long chain quaternary ammonium compounds and fatty alcohols which have been used extensively in the prior art. The positively charged ammonium moiety of long chain quaternary ammonium compounds is attracted to the negatively charged surfaces of the keratin fibers, while the long chain portions of these molecules form a coating on the hair to create a perception of smoothness and increase the manageability of the hair.
Silicones are also widely used in hair conditioner products. These products likewise form a coating on the hair shaft, and may be provided with an amino functionality or other chemical functionality to impart charge. Silicones are frequently copolymerized and co-formulated with other polymers to provide a product having a combination of attributes.
The principle sensory drawback associated with all of the prior art conditioners is that the hair tends to feel coated and heavy, driving the consumer to wash and re-style their hair more frequently, leading to further damage. In addition to silicones, the oleophilic portions of fatty alcohols and higher molecular weight quatenary compounds may cause hair to feel oily. Additionally, the majority of compounds used to provide shine properties to hair are typically oils and silicones, leading to a somewhat undesirable tactile perception over time.
Thus, there is an unmet need in the art for robust conditioning compositions that can be used to condition hair that is perceived as being damaged, without the sensory drawbacks associated with the prior art compositions.
Cationic molecules have been used extensively for various applications including hair and skin conditioning, surface modification, as wetting agents, and industrial surfactants. Fluorinated compounds have also been used in cosmetic formulations. For example, GB Application No. 1 598 567 discloses fluorinated surfactants such as Zonyl® used in combination with silicones in a hair conditioner in an effort to render the conditioner more grease resistant, i.e., less oily.
U.S. Pat. Nos. 7,763,240 and 7,785,575 (which are assigned to the assignee herein) describe fluorinated compounds useful in hair care products to control moisture penetration into the hair (frizz control). Compositions containing these compounds resist dirt, avoid a feeling of greasiness or oiliness in the hair and leave a low amount of residue (i.e., are “weightless”).
It has now been discovered that certain cationic fluorinated alcohols, which can be synthesized by the reaction of a fluorinated epoxide and a tertiary amine, have novel and beneficial effects when applied to hair. These compounds have improved deposition properties, so that they impart an improved feel to damaged, dry and coarse hair, without the sensory drawbacks associated with the prior art. More specifically, certain inventive compounds described herein have demonstrated significant deposit from rinse out formulations, leading to positive attributes such as increasing the contact angle of damaged hair, imparting shine which lasts through shampoo cycles, and reducing friction on damaged ends.
In embodiments, the compounds and compositions described herein are capable of modifying or treating surfaces including skin, hair, fabrics, solids, and may be employed as surfactants and/or surface modifying agents for improving chemical reactions.